Hydrazine hydrate (1:1) → 2-amino-3-benzyloxy-N-methylaniline

HRID 636484Notes

Reaction equation

HRID 636484 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N+:17]([O-])=O)=[C:11]([CH:14]=[CH:15][CH:16]=1)[NH:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CO>[NH2:17][C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:16][CH:15]=[CH:14][C:11]=1[NH:12][CH3:13]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 107298903-benzyloxy-2-nitro-N-methylaniline

Product 1

HCID 104895412-amino-3-benzyloxy-N-methylanilineYield 87.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 3-benzyloxy-N-methyl-2-nitroaniline (453.3 mg), 80% methanol (6.8 ml), anhydrous ferric chloride (13.6 mg) and carbon (13.6 mg) was dropwise added hydrazine monohydrate (255.6 μl), and the mixture was stirred for 5 hours at ambient temperature. Insoluble material was filtered off, and the filtrate was concentrated in vacuo. To the residue were added ethyl acetate and saturated sodium bicarbonate solution, and the separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate—n-hexane) to give 2-amino-3-benzyloxy-N-methylaniline (348.9 mg).

Workup

  1. filtrationInsoluble material was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionTo the residue were added ethyl acetate and saturated sodium bicarbonate solution
  4. washthe separated organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate—n-hexane)

Sources & evidence

ORD record
ord-a7ec7bb27e934f0e9e61ba5a67f5aef6
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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